Tetrahydrofuran → HCID 68424210, compound

HRID 1437731Notes

Reaction equation

HRID 1437731 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18](C(C)(C)C(C)C)[O:19][SiH](C)C)[NH:15][C:12]2=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.C(=O)(O)[O-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH2:18][OH:19])[NH:15][C:12]2=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 137331250HCID 137331250, compound

Product 1

HCID 68424210HCID 68424210, compoundYield 90.8%

Procedure

To the solution of 0.53 g (1.3 mmol) 5-benzyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-1H-pyrrolo[2,3-b]pyridine in 3 ml tetrahydrofuran 1.6 ml (1.6 mmol) tetra-n-butylammonium fluoride (1M solution in THF) were added. After 75 min. the solution was poured on saturated aqueous sodium bicarbonate solution and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was stirred in tert-butyl methyl ether, filtered and washed with tert-butyl methyl ether to give 0.3 g (88%) of the product as a brown solid.

Workup

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. filtrationfiltered
  7. washwashed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-9cf2fe5e23b84e9a97bc68e65b53c666
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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